Background: Labor policies and economic incentives encourage women to work beyond middle age. However, women exhibit complex patterns of workforce participation over this life stage. This study examined transitions in and out of paid work across the life course of middle-aged women over a 14-year period and investigated associations between work and chronic diseases.Methods: Latent class analysis identified dominant workforce participation patterns among 11,551 middle-aged women from the 1946–1951 birth cohort of Australian Longitudinal Study on Women's Health. Multinomial logistic regression examined associations between work patterns and chronic diseases (diabetes, asthma, depression, and arthritis), while adjusting for health risk factors, sociodemographic factors and competing activities.Results: Five latent classes were identified: “mostly in paid work” (48%), “early paid work” (9.4%), “increasingly paid work” (8.9%), “gradually not in paid work” (11.4%), and “mostly not in paid work” (22.3%). Results showed that women with chronic diseases (diabetes, asthma, depression, and arthritis) were less likely to be in paid work. These associations remained mostly unchanged after adjustments for other factors.Conclusions: The findings of this study provide better understanding of workforce participation patterns in women's late working life. This has important implications for policy design, aimed to engage middle-aged women in paid employment for longer in spite of chronic diseases and their complications. We suggest that there is a need for work place programs that support people with chronic diseases. Policies are also needed to facilitate better prevention and management of chronic health issues over the life course for women, in order to encourage workforce participation over later years.